BR112016006865A2 - substituted berberines and their syntheses - Google Patents

substituted berberines and their syntheses

Info

Publication number
BR112016006865A2
BR112016006865A2 BR112016006865A BR112016006865A BR112016006865A2 BR 112016006865 A2 BR112016006865 A2 BR 112016006865A2 BR 112016006865 A BR112016006865 A BR 112016006865A BR 112016006865 A BR112016006865 A BR 112016006865A BR 112016006865 A2 BR112016006865 A2 BR 112016006865A2
Authority
BR
Brazil
Prior art keywords
substituted
berberines
bischler
synthesis
syntheses
Prior art date
Application number
BR112016006865A
Other languages
Portuguese (pt)
Other versions
BR112016006865B1 (en
Inventor
w grote Christopher
Original Assignee
Mallinckrodt Llc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mallinckrodt Llc filed Critical Mallinckrodt Llc
Publication of BR112016006865A2 publication Critical patent/BR112016006865A2/en
Publication of BR112016006865B1 publication Critical patent/BR112016006865B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Abstract

a presente invenção refere-se a berberinas substituídas, processos para a síntese de compostos de berberina substituídos, preferencialmente, por meio de uma ciclização de bischler-napieralski seguida de redução, bem como de intermediários utilizados na síntese dos compostos de berberina substituída. o precursor de amida para a reação de bischler-napieralski poderia ser obtido pelo tratamento de amina livre haletos de ácido, fontes de formato ou aldeídos. são providos também métodos para a utilização de berberinas substituídas para inibir o crescimento de células cancerosas.The present invention relates to substituted berberines, processes for the synthesis of substituted berberine compounds, preferably by bischler-napieralski cyclization followed by reduction, as well as intermediates used in the synthesis of substituted berberine compounds. The amide precursor for the bischler-napieralski reaction could be obtained by treating free amine acid halides, formate sources or aldehydes. Methods are also provided for the use of substituted berberins to inhibit cancer cell growth.

BR112016006865-3A 2013-10-04 2014-10-02 SUBSTITUTED BERBERINES AND THEIR SYNTHESES BR112016006865B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361886695P 2013-10-04 2013-10-04
US61/886,695 2013-10-04
PCT/US2014/058806 WO2015051106A1 (en) 2013-10-04 2014-10-02 Substituted berbines and their synthesis

Publications (2)

Publication Number Publication Date
BR112016006865A2 true BR112016006865A2 (en) 2017-08-01
BR112016006865B1 BR112016006865B1 (en) 2023-05-09

Family

ID=52779136

Family Applications (1)

Application Number Title Priority Date Filing Date
BR112016006865-3A BR112016006865B1 (en) 2013-10-04 2014-10-02 SUBSTITUTED BERBERINES AND THEIR SYNTHESES

Country Status (9)

Country Link
EP (1) EP3055307B1 (en)
JP (1) JP6654568B2 (en)
AU (1) AU2014329531B2 (en)
BR (1) BR112016006865B1 (en)
CA (1) CA2923760C (en)
ES (1) ES2774775T3 (en)
MX (1) MX2016003240A (en)
PL (1) PL3055307T3 (en)
WO (1) WO2015051106A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9495155B2 (en) 2013-08-06 2016-11-15 Intel Corporation Methods, apparatus, instructions and logic to provide population count functionality for genome sequencing and alignment
JP6733449B2 (en) * 2016-09-15 2020-07-29 株式会社ツムラ Method for producing berberine alkaloid
CN109232557B (en) * 2018-11-14 2021-01-29 常州大学 Synthesis and application of 9-O-aryl substituted berberine derivative
CN114989162A (en) * 2021-02-02 2022-09-02 江苏康缘药业股份有限公司 Compound crystal form and preparation method and application thereof
CN113735847B (en) * 2021-09-10 2022-06-07 四川大学 Synthetic preparation method of berberine hydrochloride

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3272707A (en) * 1964-07-17 1966-09-13 Smith Kline French Lab Pharmaceutical compositions and methods for their use
US3420834A (en) * 1964-11-13 1969-01-07 Roussel Uclaf 2,3-dimethoxy-berbines substituted in the 10 position and process
US4013666A (en) * 1976-03-15 1977-03-22 G. D. Searle & Co. (8α,13Aβ)-8-CARBOCYCLIC/CARBOCYCLIC METHYL-5,8,13,13A-TETRAHYDRO-2,3,10,11-TETRAMETHOXY-6H-dibenzo[a,g]quinolizines and intermediates thereto
US4052389A (en) * 1976-03-23 1977-10-04 Bristol-Myers Company Derivatives of 9,10-dihydroxy-1-(p-alkoxybenzyl)-perhydroisoquinoline oxazine-3-one
US8003795B2 (en) * 2007-06-22 2011-08-23 Cvi Pharmaceuticals Limited Compounds and compositions for reducing lipid levels
EP2014651A1 (en) * 2007-07-12 2009-01-14 Exonhit Therapeutics SA Compounds and methods for modulating Rho GTPases
US8710071B2 (en) * 2008-12-23 2014-04-29 Cvi Pharmaceuticals Limited Compounds, compositions and methods for reducing lipid levels
WO2010127307A1 (en) * 2009-04-30 2010-11-04 Rutgers, The State University Of New Jersey Antimicrobial agents
WO2015191837A1 (en) * 2014-06-11 2015-12-17 Mallinckrodt Llc Oxidative dearomatization of berbines

Also Published As

Publication number Publication date
WO2015051106A1 (en) 2015-04-09
JP2016533396A (en) 2016-10-27
JP6654568B2 (en) 2020-02-26
AU2014329531A1 (en) 2016-04-14
PL3055307T3 (en) 2020-07-27
EP3055307A4 (en) 2017-08-02
CA2923760C (en) 2021-07-27
CA2923760A1 (en) 2015-04-09
AU2014329531B2 (en) 2018-04-05
EP3055307B1 (en) 2019-12-04
MX2016003240A (en) 2016-06-07
BR112016006865B1 (en) 2023-05-09
EP3055307A1 (en) 2016-08-17
ES2774775T3 (en) 2020-07-22

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Legal Events

Date Code Title Description
B25A Requested transfer of rights approved

Owner name: SPECGX LLC (US)

B07D Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette]

Free format text: DE ACORDO COM O ARTIGO 229-C DA LEI NO 10196/2001, QUE MODIFICOU A LEI NO 9279/96, A CONCESSAO DA PATENTE ESTA CONDICIONADA A ANUENCIA PREVIA DA ANVISA. CONSIDERANDO A APROVACAO DOS TERMOS DO PARECER NO 337/PGF/EA/2010, BEM COMO A PORTARIA INTERMINISTERIAL NO 1065 DE 24/05/2012, ENCAMINHA-SE O PRESENTE PEDIDO PARA AS PROVIDENCIAS CABIVEIS.

B07E Notification of approval relating to section 229 industrial property law [chapter 7.5 patent gazette]
B15K Others concerning applications: alteration of classification

Free format text: A CLASSIFICACAO ANTERIOR ERA: C07D 455/03

Ipc: C07D 455/03 (2006.01), A61P 35/00 (2006.01)

B06U Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette]
B06A Patent application procedure suspended [chapter 6.1 patent gazette]
B09A Decision: intention to grant [chapter 9.1 patent gazette]
B16A Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]

Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 02/10/2014, OBSERVADAS AS CONDICOES LEGAIS